The Road to Tuscany
Driving from Rome to Tuscany for the first-time visitor to Italy is an eye-opening experience. It is lovely to watch peoples faces as they make their way through the countryside dotted with ancient villas, hilltop towns, and fields of poppies.
They gaze in amazement, just like I still do. You just want to pinch yourself. In Australia, ancient medieval towns don’t exist. It is only something we see on TV, read in books, or imagined. The reality is so much better than what we thought it would be.
For me, and the travellers I bring, these towns, the vistas and the experiences are our dreams come true.
For those on a first-time tour of Tuscany, or for the returning traveller looking for more experiences, then I suggest you start with these beautiful towns. Each different, yet warm and welcoming and beckoning to be explored.
My suggestion would be to take your time, spend days in each one exploring, but if not possible, a day in each should give you enough of a taste, with an appetite to return.
Other articles that may interest you are:
Each of the towns I talk about in this article would make a good base from which to explore the other places. Most are accessible by train, but a car will make exploring easier.
Or you can book one of the many tours available and learn more from the local tour guide than you would on your own. Whatever you choose, you will not be disappointed. These towns are the epitome of Tuscany, and I have no doubt you will enjoy them all.
No time to read? Save to Pinterest and enjoy later.
Ok, I know. Orvieto is not actually in Tuscany, but just over the border in Umbria. But I promise you will not notice the difference.
The reason we have included Orvieto is that if you were coming from Rome then you would stumble upon Orvieto first and I think it is a town that should not be missed.
Located 1.5 hours train ride from Rome or almost 2-hours by car. You can also see read my One Day Complete Guide to Orvieto which will give you details on how to get around and what to do.
Things to Do
Orvieto sits perched high on the hilltop overlooking the countryside below. The Duomo is a spectacular site and can be seen from some locations in the distance standing tall above the town.
Orvieto can be seen easily walking from end to end. Don’t forget to visit the Duomo and I highly recommend an Orvieto Underground Tour where you can see the maze of tunnels and caves that remain intact beneath the town.
Climb Torre del Moro where you will be able to take in the 360-degree view of the city. And don’t forget St Patrick’s Well, an interesting site to visit with 496 down. Remember what goes down must come back up, but it’s an excellent workout for the legs!
You can purchase the Carta Unica for €20. The card will allow you entry into 11 museums and monuments including St Patrick’s Well, Torre del Moro, the Duomo and Orvieto Underground. A great way to save if you plan on visiting a number of sites.
You can find out more about Carta Unica here where you can also download the map and find out where to purchase your card.
Spend some time browsing in the quaint stores. You will find a good variety of shops including leather handbags and unique Orvieto ceramics. If you happen to be visiting on a Thursday or Saturday, you will find the markets in full swing selling everything from produce to clothing.
And don’t forget to buy a bottle or two of the Orvieto Classico and the Rosso Orvietano to take. Both are delicious.
Orvieto is easy to get to by train. Once you arrive at the station you will find the furnicular directly across the road that will take you to the top.
If you want the ease of a tour that will include Orvieto then see below for some good options. Seeing the hilltop towns of Tuscany and Umbria is not always easy without a car and a tour can be an excellent way of seeing the best places.
Looking down into St Patrick’s Well
Montepulciano is a medieval hilltop town located in the south of Tuscany.
It is a lovely town to visit for a day trip but is a bit more difficult to get to by train. You will also need to catch the bus. This area is easier to explore by car, or like I did, on a tour.
It is two hours by car from Rome and almost 40 minutes from Cortona. It will take around an hour by car from Orvieto.
Things to Do
Montepulciano is a hilltop town so be prepared for a little bit of walking, but it is the only way to see the town and the magnificent sweeping views of the landscape below.
Find your way through the Piazza Grande, past the Palazzo del Comune and Cathedral of Santa Maria, the old Fortress and look down over the city walls and see the Church of San Biagio.
Do some shopping in the cute little stores and get lost exploring laneways.
And of course, don’t forget to stop for a spot of wine tasting.
Montepulciano is known for its Vino Nobile di Montepulciano. DO NOT leave this beautiful town without tasting it!
You can find a number of places for wine tasting. We participated in a tour of Cantina Ercolani, one of the ancient cantinas built under the city. As well as the delicious wine to taste, it was an interesting place to visit. There was no pressure to buy wine either. Highly recommended.
Later in our trip, we enjoyed an afternoon sharing the bottle of Vino Nobile di Montepulciano we bought on tour. We sat in the courtyard of our villa happily sipping away and savouring every mouthful. Apparently, there are photos lurking somewhere (sorry I couldn’t find them) of how much we enjoyed this wine. I don’t remember laughing as much as I did that day.
I thoroughly enjoyed a tour I joined that picked us up in Cortona and visited Montepulciano where we enjoyed some wine tasting, Pienza where we had lunch at a lovely restaurant (see below), onto Montalcino, stopping at the Abbey and finishing with another wine tasting before heading back to Cortona. Joining a tour allowed us to see all these places we would not have been able to visit without a car, and Laura our guide was fantastic. Researching information on new destinations is fun, but there is nothing quite like having a local guide to tell you all the stories and history of the area.
Church of San Biagio
Wine Tour at Cantina Ercolani
Take a look at part of the tour we took in Montepulciano. You can hear our tour guide Laura talking. Apologies for the shaky video.
YOU MIGHT ALSO LIKE: How to Experience Florence, Your Way
Cortona is very special. I stayed here with a group for six days, and I could have stayed longer.
It is a 2.5-hour train ride from Rome and about the same time if you decide to drive. Please note that if you drive you will need to park outside the city walls. You can see the parking areas on the map below.
The train station is located below the town and you will need to catch a bus to take you up, or it is easy to organise a taxi.
Things to Do
For more on my recommendations, you can also read A Tuscan Town called Cortona which highlights my stay in Cortona.
Cortona is small enough to walk from city wall to city wall and take in the breathtaking views. From Piazza Garibaldi, you can gaze over the valley below and all the way to Lake Trasimeno.
Visit the Church of Santa Margherita and the Fortress that sit high above the town. It is a bit of a walk but manageable.
Take time to sit in Piazza della Repubblica at a café, people watching. Enjoy some shopping from the array of stores available and perhaps a visit to the Etruscan Museum.
Visit the Parterre Gardens, and if you walk to the end of the parkway, you can catch a glimpse of “Bramasole”, the villa bought by Frances Mayes, author of Under the Tuscan Sun.
Time allowing, I recommend you visit Le Celle, a Franciscan Monastery not far from Cortona. For those without a car, you can easily arrange for a taxi to take you there.
If you only have one day here and are not too sure what you should see and do you can get a complete itinerary here – One Day in Cortona.
Looking towards Piazza della Repubblica
View from Piazza Garibaldi
YOU MIGHT ALSO LIKE: The Best of Verona
Want to see more?
If you have time and want to see more beautiful towns then we suggest you add these towns to your itinerary:
Sadly I did not get to explore Montalcino. We stopped below the town as part of our tour. Our only stop was at the Abbey of Sant’Antimo.
Given its high position, Montalcino looks down over valleys filled with olive groves and vineyards.
It is also known for its wine, Brunello di Montalcino. This is wine to savour. I don’t know a lot about wines, but I do know that this one is magnificent. I thoroughly enjoyed sipping my way through a glass or two at our villa during Happy Hour. Heaven!
Our visit to the Abbey was a complete surprise. All I can say is please go.
It is beautiful and different from any of the other churches I visited. It has a simplicity and serenity that I find hard to describe, but if you are in the area, you must go. Promise?
Abbey of Sant’Antimo
I didn’t spend as much time in Pienza as I would have liked, which was such a shame. And I would like to tell you more about it, but I would only be telling you what you can glean from other websites and other articles anyway.
But I did want to recommend it because the next time I am in Tuscany, I would like to go back and explore.
Situated in the Val d’Orcia region, Pienza is a delightful hilltop town (another one!) located between Montepulciano and Montalcino. It is brimming with character and recognized as a UNESCO World Heritage Site because of the significance of the town.
“as it represents the first application of the Renaissance Humanist concept of urban design…” – UNESCO
We did have lunch at La Buca di Enea which was divine. I highly recommend you try it. The owner is quite a character and the food was fantastic. I can highly recommend the Pig Livers and Wild Boar. Yum! They even catered to our gluten free requirements and provided us with the best gluten-free bread rolls I have ever tasted.
Food is wonderful here. The owner is a character!
Learn my EASY & STRESS-FREE planning method for creating the PERFECT TRAVEL ITINERARY. Free download right here!
Planning your Stay
If you are planning on exploring all of these lovely towns, then this is the route I would recommend.
Rome – Orvieto – Montepulciano – Pienza – Montalcino – Cortona
Stay for a day in each one, stay in some and visit others, but whatever you choose to do you will love touring the countryside of this beautiful part of Italy.
You know all those gorgeous photos you see depicting Tuscany? Yep, this is where you will see them. Get ready for your jaw to hit the floor and have your camera poised and ready!
Another one for Pinterest
Affiliate links were used in this post. By using the links in this article, we receive a small commission, at no extra cost to you, so that we can continue to provide free helpful content. Thank you. We appreciate your support.
YOU MIGHT ALSO ENJOY THESE